Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
Simple Synthesis of Mite Pheromone β-Acaridial and Its Analogs in the Secretion of Caloglyphus polyphyllae (Acari: Acaridae)
Nobuhiro SHIMIZUNaoki MORIYasumasa KUWAHARA
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2003 年 67 巻 8 号 p. 1732-1736

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  A simple synthesis of β-acaridial [(E)-1], the active principle of the sex, alarm and aggregation pheromone among astigmatid mites, was achieved in 5 steps from 1,2,4-butanetriol 2 in a 19% overall yield. Its analog, β-acariolal 8, was also prepared in a 63% yield by oxidation of the intermediate, β-acaridiol [(E)-7], with pyridinium dichromate (PDC). This synthetic route also gave β-(Z)-acaridiol [(Z)-7] by using a Z-selective base in the Wittig reaction. (Z)-7 was oxidized to give a new monoterpene, β-(Z)-acaridial [(Z)-1], which was detected as a trace component in the secretion of Caloglyphus polyphyllae, together with 8.
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© 2003 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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